Anellated (OXA) hydantoines and their use as herbicides

ABSTRACT

The invention relates to new anellated (oxa)hydantoins, and herbicidal compositions containing same. The invention also relates to methods for controlling noxious plants using the anellated (oxa)hydantoins of the invention.

This is a division of application Ser. No. 08/374,782, filed Apr. 21,1995, now U.S. Pat. No. 5,661,109 which is the national stageapplication of PCT/EP93/02026, filed Jul. 29, 1993, under 35 U.S.C. 371.

The present invention relates to new anellated (oxa)hydantoins of theformula I ##STR1## wherein R¹ to R⁴ and Q have the meaning given in thedescription, a method for their preparation and their use as herbicides.

As has already been communicated, certain thiohydantoins (see EP-A2 0290 902) or heterocyclic imides (see EP-A1 272 594, EP-B1 0 070 389) canbe used as herbicides.

Surprisingly, new bicyclic imides have now been found which possess adistinctly better herbicidal action and excellent selectivity.

The present invention therefore comprises compounds of the formula I##STR2## wherein R¹ and R², independently of one another, representhydrogen or a group of the series (C₁ -C₄) alkyl, (C₁ -C₂) haloalkyl orphenyl, which is optionally fluorine-substituted,

R³ and R⁴, independently of one another, represent hydrogen, (C₁ -C₄)alkyl, phenyl, both optionally fluorine-substituted, and/or clorine-,bromine- or methyl-substituted, (C₁ -C₄) alkoxy; or also together form acarbocyclic ring which may optionally be (C₁ -C₄) alkyl-substituted,

Q represents one of the radicals Q₁ -Q₇ ##STR3## wherein W represents Oor S,

R⁵ represents hydrogen or halogen,

R⁶ represents (C₁ -C₂) alkyl (C₁ -C₂) haloalkyl, OCH₃, SCH₃, OCHF₂,halogen, CN or NO₂,

R⁷ represents hydrogen, (C₁ -C₈) alkyl, (C₁ -C₈) haloalkyl, halogen,OR¹¹, S(O)_(n) R¹¹, COR¹¹, CO₂ R¹¹, C(O)SR¹¹, C(O)NR¹² R¹³, CHO,CH═CHCO₂ R¹¹, CO₂ N═CR¹⁴ R¹⁵, NO₂, CN, NHSO₂ R¹⁶ or NHSO₂ NHR¹⁶,

R⁸ represents hydrogen, (C₁ -C₃) alkyl, (C₁ -C₃) haloalkyl or halogen,

R⁹ represents hydrogen, (C₁ -C₃) alkyl, (C₁ -C₃) haloalkyl or halogen;or if Q is Q-2 or Q-6, R⁸ and R⁹ together with the carbon atom to whichthey are bonded can be C═O;

R¹⁰ represents (C_(1-C) ₆) alkyl, (C₁ -C₆) haloalkyl, (C₂ -C₆)alkoxyalkyl, (C₃ -C₆) alkenyl or (C₃ -C₆) alkynyl,

R¹¹ represents (C₁ -C₈) alkyl, (C₃ -C₈) cycloalkyl, (C₃ -C₈) alkenyl,(C₃ -C₈) alkynyl, (C₁ -C₈) haloalkyl, (C₂ -C₈) alkoxyalkyl, (C₂ -C₈)alkylthioalkyl, (C₂ -C₈) alkylsulphinyl alkyl, (C₂ -C₈)alkylsulphonylalkyl, (C₃ -C₈) alkoxyalkoxyalkyl, (C₄ -C₈)cycloalkylalkyl, (C₂ -C₄) carboxyalkyl, (C₃ -C₈) alkoxycarbonylalkyl,(C₆ -C₈) alkenyloxycarbonylalkyl, (C₆ -C₈) alkynyloxycarbonylalkyl, (C₄-C₈) alkenoxyalkyl, (C₆ -C₈) cycloalkoxyalkyl, (C₄ -C₈) alkynyloxyalkyl,(C₃ -C₈) haloalkoxyalkyl, (C₄ -C₈) haloalkenyloxyalkyl, (C₄ -C₈)haloalkynyloxyalkyl, (C₆ -C₈) cycloalkyl-thioalkyl, (C₄ -C₈)alkenylthioalkyl, (C₄ -C₈) alkynlylthioalkyl, (C₁ -C₄) alkyl-substitutedwith phenoxy or benzyloxy, which may both optionally be halogen-, (C₁-C₃) alkyl- or (C₁ -C₃) haloalkyl-substituted; (C₄ -C₈)trialkylsilylalkyl, (C₃ -C₈) cyanoalkyl, (C₃ -C₈) halocycloalkyl, (C₃-C₈) haloalkenyl, (C₅ -C₈) alkoxyalkenyl, (C₅ -C₈) halo-alkoxyalkenyl,(C₅ -C₈) alkylthioalkenyl, (C₃ -C₈) haloalkynyl, (C₅ -C₈) alkoxyalkynyl,(C₅ -C₈) haloalkoxyalkynyl, (C₅ -C₈) alkythioalkynyl, (C₂ -C₈)alkylcarbonyl, benzyl optionally substituted with halogen, (C₁ -C₃)alkyl or (C₁ -C₃) haloalkyl; CHR¹⁷ COR¹⁸, CHR¹⁷ P(O) (OR¹⁸)₂, P(O)(OR¹⁸)₂, CHR¹⁷ P(S) (OR¹⁸)₂, CHR¹⁷ C(O)NR¹² R¹³, CHR¹⁷ C(O) NH₂, phenylor pyridyl, both optionally substituted with halogen, (C₁ -C₃) alkyl,(C₁ -C₃) haloalkyl or (C₁ -C₄) alkoxy,

R¹² and R¹⁴, independently of one another, represent hydrogen or (C₁-C₄) alkyl,

R¹³ and R¹⁵, independently of one another, represent (C₁ -C₄) alkyl,phenyl, optionally substituted with halogen, (C₁ -C₃) alkyl, (C₁ -C₃)haloalkyl or (C₁ -C₄) alkoxy, or

R¹² and R¹³ may be combined into rings as --(CH₂)₅ --, --(CH₂)₄ --, or--CH₂ CH₂ OCH₂ CH₂ --, wherein one or more H atoms in each ring may besubstituted optionally by (C₁ -C₃) alkyl, phenyl or benzyl;

R¹⁴ and R¹⁵ together with the carbon atom to which they are bonded canform a (C₃ -C₈) cycloalkyl group,

R¹⁶ represents (C₁ -C₄) alkyl or (C₁ -C₄) haloalkyl,

R¹⁷ represents hydrogen or (C₁ -C₃) alkyl,

R¹⁸ represents (C₁ -C₆) alkyl, (C₃ -C₆) alkenyl or (C₃ -C₆) alkynyl, and

n represents 0, 1, 2.

In the definitions given above, the term "alkyl", alone or in thecompound term as "alkylthio" or "haloalkyl", includes a linear orbranched chain, for example, methhyl, ethyl n-propyl, isopropyl or thevarious butyl isomers. Alkoxy includes menthoxy, ethoxy, n-propyloxy,isopropyloxy- and the different butyl isomers. Alkenyl includes linearor branched alkenes, for example, 1 -propenyl, 2-propenyl, 3-propenyland the different butyl isomers. Cycloalkyl includes cyclopropyl,cyclobutyl, cyclopentyl and cyclohexyl. The term "halogen", alone or inthe compound term as "haloalkyl" signifies fluorine, chlorine, bromineor iodine. In addition, when "haloalkyl" is used in the compound term,then "alkyl" may be partially or wholly substituted by halogen atoms,which in their turn may be identical or different. Examples of haloalkylinclude CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFCl.

The following radicals are preferred, wherein

R¹ and R², independently of one another, represent hydrogen or a groupof the series (C₁ -C₄) alkyl, (C₁ -C₂) haloalkyl or phenyl, which isoptionally fluorine-substituted,

R³ and R⁴, independently of one another, represent hydrogen, (C₁ -C₃)alkyl, phenyl, optionally fluorine-substituted and/or chlorine-,bromine-, methyl-substituted, (C₁ -C₂) alkoxy; or together form acarbocyclic ring which may optionally be (C₁ -C₂) alkyl-substituted,

Q signifies ##STR4## wherein W represents O or S,

n represens 0, 1, 2,

R⁵ represents hydrogen or halogen,

R⁶ represents halogen or CN,

R⁷ represents hydrogen, (C₁ -C₄ ) alkyl, (C₁ -C₄) haloalkyl, halogen,OR¹¹, S(O)_(n) R¹¹, COR¹¹, CO₂ R¹¹, C(O)SR¹¹, C(O)NR¹² R¹³, CH═CHCO₂R¹¹, CO₂ N═CR¹⁴ R¹⁵, NHSO₂ R¹⁶ or NHSO₂ NHR¹⁶,

R⁸ represents hydrogen, (C₁ -C₃) alkyl or (C₁ -C₃) haloalkyl,

R⁹ represents hydrogen, (C₁ -C₃) alkyl or (C₁ -C₃) halolakyl; or

if Q is Q-2 or Q-6, R⁸ and R⁹ together with the carbon atom to whichthey are bonded can be C═O;

R¹⁰ represents (C₁ -C₄) alkyl, (C₁ -C₄) haloalkyl, (C₂ -C₄) alkoxyalkyl,(C₃ -C₆) alkenyl or (C₃ -C₆) alkynyl,

R¹¹ represents (C₁ -C₄) alkyl, (C₃ -C₆) cycloalkyl, (C₃ -C₆) alkenyl,(C₃ -C₆) alkynyl, (C₁ -C₄) haloalkyl, (C₂ -C₄) alkoxyalkyl, (C₂ -C₄)alkylthioalkyl, (C₂ -C₄) alkylsulphinyl-alkyl, (C₂ -C₄)alkylsulphonylalkyl, (C₃ -C₆) alkoxyalkoxyalkyl, (C₄ -C₈)cycloalkylalkyl, (C₂ -C₄) carboxyalkyl, (C₃ -C₆) alkoxycarbonylalkyl,(C₆ -C₈) alkenyloxycarbonylalkyl, (C₆ -C₈) alkynyloxycarbonylalkyl, (C₄-C₆) alkenoxy-alkyl, (C₆ -C₈) cycloalkoxyalkyl, (C₄ -C₆)alkynyloxyalkyl, (C₃ -C₆) haloalkoxyalkyl, (C₄ -C₈) haloalkenyloxyalkyl,(C₄ -C₆) haloalkynyloxyalkyl, (C₆ -C₈) cycloalkyl-thioalkyl, (C₄ -C₆)alkenylthioalkyl, (C₄ -C₆) alkynylthioalkyl, (C₁ -C₂) alkyl-substitutedwith phenoxy or benzyloxy, which may both optionally be halogen-, (C₁-C₃) alkyl- or (C₁ -C₃) haloalkyl-substituted; (C₄ -C₈)trialkylsilylalkyl, (C₃ -C₄) cyanoalkyl, (C₃ -C₆) halocycloalkyl,(C_(3-C) ₆) haloalkenyl, (C₅ -C₆) haloalkoxyalkenyl, (C₅ -C₆)alkylthioalkenyl, (C₃ -C₆) haloalkynyl, (C₅ -₆) alkoxyalkynyl, (C₅ -C₆)haloalkoxyalknyl, (C₅ -₆) alkylthioalkynyl, (C₂ C₄) alkylcarbonyl,benzyl optionally substituted with halogen, (C₁ -C₂) alkyl or (C₁ -C₂)haloalkyl; CHR¹⁷ COR¹⁸, CHR¹⁷ P(O)(OR¹⁸)₂, P(O)(OR¹⁸)₂, CHR¹⁷ P(S)(OR¹⁸)₂, CHR¹⁷ C(O)NR¹² R¹³, CHR¹⁷ C(O)NH₂, phenyl or pyridyl, bothoptionally substituted with halogen, (C₁ -C₃) alkyl, (C₁ -C₃) haloalkylor (C₁ -C₄) alkoxy,

R¹² and R¹⁴, independently of one another, represent hydrogen or (C₁-C₂) alkyl,

R¹³ and R¹⁵, independently of one another, represent (C₁ -C₂) alkyl,phenyl, optionally substituted with halogen, (C₁ -C₂) alkyl, (C₁ -C₂)haloalkyl or (C₁ -C₂) alkoxy, or

R¹² and R¹³ may be combined into rings as --(CH₂)₅ --, --(CH₂)₄ --, or--CH₂ CH₂ OCH₂ CH₂ --, wherein one or more H atoms in each ring may besubstituted optionally by (C₁ -C₂) alkyl, phenyl or benzyl;

R¹⁴ and R¹⁵ together with the carbon atom to which they are bonded canform a (C₃ -C₆) cycloalkyl group,

R¹⁶ represents (C₁ -C₄) alkyl or (C₁ -C₄) haloalkyl,

R¹⁷ represents hydrogen or (C₁ -C₃) alkyl,

R¹⁸ represents (C₁ -C₄) alkyl, (C₃ -C₄) alkenyl or (C₃ -C₄) alkynyl.

The following radicals are preferred, wherein

R¹ and R², independently of one another, represent hydrogen or a groupof the series (C₁ -C₃) alkyl, (C₁ -C₂) haloalkyl or phenyl, which isoptionally fluorine-substituted,

R³ and R⁴, independently of one another, represent hydrogen, (C₁ -C₃)alkyl, or also together form a 5- to 6-membered carbocyclic ring, whichmay optionally substituted with (C₁ -C₄) alkyl radicals,

Q signifies ##STR5## wherein W represents O or S,

n represents 0, 1, or 2,

R⁵ represents hydrogen, fluorine or chlorine,

R⁶ represents chlorine, bromine or cyanogen,

R⁷ represents hydrogen, OR¹¹ or CO₂ R¹¹,

R⁸ and R⁹, independently of one another, represent hydrogen, (C₁ -C₂)alkyl or (C₁ -C₂) haloalkyl,

R¹⁰ represents (C₁ -C₂) alkyl, (C₁ -C₂) haloalkyl, (C₃ -C₄) alkenyl or(C₃ -C₄) alkynyl,

R¹¹ represents (C₁ -C₄) alkyl, (C₃ -C₆) cycloalkyl, (C₃ -C₆) alkenyl,(C₃ -C₆) alkynyl, (C₁ -C₄) haloalkyl, (C₂ -C₄) alkoxyalkyl, (C₂ -C₄)alkylthioalkyl, (C₂ -C₄) alkylsulphinylalkyl, (C₂ -C₄)alkylsulphonylalkyl, (C₃ -C₆) alkoxyalkoxyalkyl, (C₄ -C₈)cycloalkylalkyl, (C₂ -C₄) carboxyalkyl, (C₃ -C₆ ) alkoxycarbonylalkyl,(C₆ -C₈) alkenyloxycarbonylalkyl, (C₆ -C₈) alkynyloxycarbonylalkyl, (C₆-C₈) cyclo-alkoxyalkyl, (C₄ -C₆) alkenyloxyalkyl, (C₄ -C₆)alkynyloxyalkyl, (C₃ -C₆) haloalkoxyalkyl, (C₄ -C₈) haloalkynyloxyalkyl,(C₄ -C₆) haloalkynyloxyalkyl, (C₆ -C₈) cycloalkyl-thioalkyl, (C₄ -C₆)alkenylthioalkyl, (C₄ -C₆) alkynylthioalkyl, (C₁ -C₂) alkyl-substitutedwith phenoxy or benzyloxy, which are both optionally substituted withhalogen-, (C₁ -C₃) alkyl- or (C₁ -C₃) haloalkyl; ( C₄ -C₈)trialkylsilylalkyl, (C₃ -C₄) cyanoalkyl, (C₃ -C₆) halocycloalkyl, (C₃-C₆) haloalkenyl, (C₅ -C₆) alkoxyalkenyl, (C₅ -C₆) haloalkoxyalkenyl,(C₅ -C₆) alkylthioalkenyl, (C₃ -C₆) haloalkynyl, (C₅ -C₆) alkoxyalkynyl,(C₅ -C₆) alkylcarbonyl, (C₅ -C₆) alkylthioalkynyl, (C₂ -C₄)alkylcarbonyl, benzyl optionally substituted with halogen, (C₁ -C₂)alkyl or (C₁ -C₂) haloalkyl; CHR¹⁷ COR¹⁸, CHR¹⁷ P(O) (OR¹⁸)₂, P(O)(OR¹⁸)₂, CHR¹⁷ P(S) (OR¹⁸)₂, CHR¹⁷ C(O)NR¹² R¹³, CHR¹⁷ C(O)NH₂, phenylor pyridyl, both optionally substituted with fluorine, chlorine orbromine, (C₁ -C₂) haloalkyl or (C₁ -C₂) alkoxy,

R¹² represents hydrogen or (C₁ -C₂) alkyl,

R¹³ represents (C₁ -C₂) alkyl, phenyl optionally substituted withfluorine, chlorine, bromine, (C₁ -C₂) alkyl, (C₁ -C₂) haloalkyl or (C₁-C₂) alkoxy, or

R¹² and R¹³ may be combined into rings as --(CH₂)₅ --, --(CH₂)₄ --, or--CH₂ CH₂ OCH₂ CH₂ --, wherein one or more H atoms in each ring may besubstituted optionally by (C₁ -C₂) alkyl,

R¹⁷ represents hydrogen or (C₁ -C₂) alkyl,

R¹⁸ represents (C₁ -C₂) alkyl, (C₃ -C₄) alkenyl or (C₃ -C₄) alkynyl.

The following radicals are preferred, wherein

R¹ and R², independently of one another, represent hydrogen, (C₁ -C₃)alkyl (C₁ -C₂) haloalkyl or phenyl,

R³ and R⁴, independently of one another, represent hydrogen or (C₁ -C₃)alkyl, or together form a 5- to 6-membered carbocyclic ring.

Q signifies ##STR6## wherein R⁵ represents fluorine or chlorine,

R⁶ represents chlorine,

R⁷ represents OR¹¹ or CO₂ R¹¹,

R¹¹ represents (C₁ -C₄) alkyl, (C₃ -C₆) cycloalkyl, (C₃ -C₆) alkenyl,(C₃ -C₄) alkynyl, (C₁ -C₃) haloalkyl, (C₂ -C₄) alkoxyalkyl, (C₃ -C₆)alkoxycarbonylalkyl, (C₆ -C₈) alkenyl-oxycarbonylalkyl or (C₆ -C₈)alkynyloxycarbonyl.

The present invention relates both to the possible individualstereoisomers of the formula I and to mixtures of the isomers. Thestereoisomers having the 2R, 3S configuration are preferred to others.

The new anellated (oxa)hydantoins of the general formula I are obtainedaccording to the present invention by a general method A, when arylisocyanates of the general formula II

    Q--N═C═O                                           II

wherein

Q has the meanaing given above, and

oxazolidine carboxylic acid (ester) of the general formula III ##STR7##wherein R¹, R², R³ and R⁴ (R³ =R⁴ ≠H) have the meaning given above and Ris H, (C₁ -C₄) alkyl or active ester, are reacted together according tomethod A optionally in the presence of an acid acceptor and optionallyin the presence of a diluent.

The invention also provides a method B for preparing compounds of theformula I, which is illustrated below, and wherein R¹ to R⁴ and Q havethe above meanings, wherein a compound of the formula III, wherein Rstands for H and ##STR8## which can be prepared under equilibriumconditions from compounds of the formula IV and compounds of the formulaV or salts thereof optionally in the presence of an acid acceptor andoptionally in the presence of a diluent, is reacted with a compound fthe formula II optionally in the presence of an acid acceptor andoptionally in the presence of a diluent, in order to obtain compounds ofthe formula VI, wherein R is H, (C₁ -C₄) alkyl or an active ester##STR9## which can then be converted by ring closure into compounds ofthe formula I.

The invention also provides a method C for preparing compounds of theformula I, which is illustrated below, and wherein R¹ to R⁴ have theabove meanings. To this end a compound of the formula III, wherein Rstands for H or (C₁ -C₄) alkyl, is reacted with phosgene or a phosgenesubstitute, with first of all compounds of the formula VII being formed,which latter compounds are then reacted with compounds of the formulaVIII, wherein Q has the meaning given above, in order to obtaincompounds of the formula VI, ##STR10## which can then be converted byring closure into compounds of the formula I.

The invention also provides a method D for preparing compounds of theformula I, which is illustrated below, and wherein R¹ to R⁴ and Q havethe above meanings, wherein a compound of the formula II is reacted witha compound of the formula IX, optionally in the presence of an acidacceptor and optionally in the presence of a diluent, in order to obtaincompounds of the formula X, and the compounds, X thus obtained ##STR11##are then hydrolysed and converted by ring closure into compounds of theformula I.

The present invention also provides a method E for preparing compoundsof the formula I, wherein the compounds of the formula XI ##STR12##wherein R¹ to R⁶ have the meanings given above and X signifies O, S orNH, are reacted with a halide of the formulae XII, XIII or XIV,##STR13## wherein Z is an atom or chlorine, bromine or iodine and R¹¹and R¹⁶ have the meanings given above.

Finally it has been found that the new anellated (oxa)hydantoins of thegeneral formula I possess outstanding herbicidal properties.

In the method A, in the case where R represents alkyl, the reaction isconducted in an inert organic solvent, for example, in an aromaticsolvent such as toluene, chlorobenzene; a halogenated hydrocarbon suchas chloroform or methylene chloride; an ether such as diisopropyl ether;or in acetonitrile or dimethylformamide, optionally base-catalysed attemperatures of between 20° and 120° C. Preferably organic bases areused, for example, organic amines such as triethylamine or pyridine (seeEP-A1 0 272 594). Variants of the general method A are described inEP-A2 0 070 389.

In the method B, which has proved successful particularly in cases whereR³ and R⁴ represent H, the reaction proceeds in water as solvent or,preferably, in the two-phase system water/organic solvents. Particulalypreferred is the method of operation whereby compounds of the formulaeIV and V, optionally salts of V, are added to an inorganic base, forexample, an alkali metal hydroxide or alkaline earth metal hydroxide,carbonate or hydrogen carbonate such as sodium hydroxide or potassiumcarbonate, or to an organic base, for example, an organic amine such astriethylamine, and then maintained for several days, preferably 3 to 10h, at a temperature of between -40° and +50° C., preferably between -10°and +10° C.

The compound of the formula III is formed in this aqueous solution inequilibrium. To it the isocyanate of the formula II, dissolved in aninert organic solvent, for example, toluene, chlorobenzene orchloroform, is added dropwise with vigorous stirring.

The ph-value of the aqueous phase is then established at between 1 and 3by means of acid, preferably an inorganic acid such as aqueoushydrochloric acid or sulphuric acid. The urea derivatives of the formulaVI thus arising are then formed into rings by known methods at atemperaturc of between 50° and 100° C. or, optionally, by conversioninto an ester (R stands for alkyl or active ester) (see Houben-Weyl,Methoden der Organischen Chemie, volume XXV/1 and XXV/2 (1974)).

The compounds of the formula II are known or can be prepared analogouslyby known methods; see Houben-Weyl, methoden der Organischen Chemie,volume VIII, page 120 (1952); Houben-Weyl, volume IX, pages 875, 869(1955); EP-B1 0 070 389; U.S Pat. No. 4, 881, 967; EP-A1 322 401; U.S.Pat. No. 3, 495, 967; EP-A2 300 307; EP-A2 349 832.

Amines of the formula III are known and for R³ =R⁴ ≠H can be preparedanalogously to known methods see, for example D. Seebach et al., Helv.Chim. Acta, volume 70, 1194 (1987).

Amines or the general tormula IX are known or can be prepared accordingto EP-A 3 073 569 or in a manner analogous to the methods describedthere.

The present invention also relates to the use of the compounds of theformula I as herbicides as well as herbicidal compositions which containan effective content of a compound of the formula I and a carrier.Carriers are preferably surface-active substances, solid or liquiddiluents.

The invention also relates to a method for controlling noxious plants,wherein a herbicidally effective quantity of a compound according toformula I is applied to the noxious plants or to their environment(prior to or after germination).

CHEMICAL EXAMPLES Example 1 ##STR14## A mixture of 2,2-dimethyloxazolidine-4-carboxylic methyl ester (1.99 g, 0.01 mol),triethylamine (50.0 mg, 0.5 mmol) and toluene (30 ml) is prepared, towhich 4-chlorphenyl isocyanate (1.40 g, 0.009 mol) dissolved in 20 ml oftoluene is added dropwise. The reaction mixture is stirred at 200° C.for 15 h and then washed with 10% aqueous hydrochloric acid (3×10 ml)and water (3 ×10 ml) , dried over sodium sulphate and filtered. Afterconcentrating the filtrate by evaporation, the residue is dissolved indiethyl ether and reprecipitated from petroleum ether.

2.28 g (81% of the theoretical quantity) of 7-(4-chlorophenyl) -5,5-dimethyl-6, 8-dioxo-4-oxa-1, 7-diazabicyclo 3.3.0!octane having amelting point of 97°-98° C. is obtained.

Example 2 ##STR15## A mixture of serine (1.05 g, 0.01 mol) 37% aqueousformaldehyde solution (2 g) and aqueous sodium hydroxide solution (10ml) is maintained at 4° C. for 12 h, cooled to 0° C., then4-chlorophenyl isocyanate (1.55 g) dissolved in chlorobenzene (5 ml) isadded dropwise. The reaction mixture is then stirred at 0°-5° C. for 1/2h and at room temperature for approximately 2 h, the aqueous phase isextracted by shaking with chloroform (3×10 ml) and the collected organicphases are discarded.

The aqueous phase is then acidified to ph 1 with 5% aqueous hydrochloricacid and the product is introduced into the organic phase by shakingwith ethyl acetate (3×10 ml), dried over sodium sulphate and filtered.After concentrating the filtrate by evaporation, the residue is taken upin acetonitrile (25 ml) and reacted with N-hydroxysuccinimide (1.15 g,0.01 mol) . N, N'-diclohexyl carbodiimine (2.06 g, 0.01 mol), dissolvedin acetonitrile (15 ml), is then added dropwise at 20° C. The reactionmixture is stirred for 12 h under reflux, then filtered and the filtrateis concentrated by evaporationv The remainig residue is taken up in alittle acetone and again precipitated with water.

7-(4-chlorophenyl) -6, 8-dioxo-4-oxa-1, 7-diazabicyclo 3.3.0!octanehaving a melting point of between 74° to 76° C. is obtained in aquantity of 1.75 g (74% of the theoretical quantity).

The compounds of the general formula I shown in the following tables canbe prepared analogously to Examples 1 and 2 and in accordance with thegeneral description of methods A to E according to the presentinvention.

                                      TABLE 1                                     __________________________________________________________________________     ##STR16##                                                                                                       Melting                                    R.sup.1                                                                         R.sup.2                                                                            R.sup.3                                                                            R.sup.4                                                                          R.sup.5                                                                         R.sup.6                                                                          R.sup.7        point °C.                           __________________________________________________________________________    H H    nC.sub.3 H.sub.7                                                                   CH.sub.3                                                                         H Cl H              88-94                                      H H    C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  H Cl H              112-114                                    H H    C(CH.sub.3).sub.3                                                                  H  H Cl H              112-114                                    H H    C.sub.6 H.sub.5                                                                    CH.sub.3                                                                         H Cl H              138-139                                    H H    (CH.sub.2).sub.4                                                                   -- H Cl H              127-128                                    H H    (CH.sub.2).sub.5                                                                   -- H Cl H                141-141.5                                H H    (CH.sub.2).sub.5                                                                   -- H Br H                                                         H H    (CH.sub.2).sub.5                                                                   -- Cl                                                                              Cl H                                                         H H    (CH.sub.2).sub.6                                                                   -- H Cl H              87-89                                      H H    (CH.sub.2).sub.6                                                                   -- F Cl H                                                         H H    (CH.sub.2).sub.5                                                                   -- F Cl CO.sub.2 CH(CH.sub.3).sub.2                                                                  glass-like                                 H H    CH.sub.3                                                                           CH.sub.3                                                                         F Cl CO.sub.2 CH(CH.sub.3).sub.2                                                                  glass-like                                 H CH.sub.3                                                                           (CH.sub.2).sub.6                                                                   -- H Cl H              95-97                                      H H    H    H  Cl                                                                              Cl H                                                         H H    H    H  H Cl H              74-76                                      H H    H    H  Cl                                                                              Cl Cl                                                        H H    H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                                                                  89-91                                                                         (1 isomer)                                 H H    H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                                                                  Resin                                                                         (2 isomer)                                 H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                                                                  glass-like                                                                    (1 isomer)                                 H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                                                                  Resin                                                                         (2 isomer)                                 H CH.sub.3                                                                           H    H  H Cl H              96-98                                      H H    H    H  F Cl OCH.sub.3      172-175                                    H H    H    H  F Cl OCH(CH.sub.3).sub.2                                                                          glass-like                                 H CH.sub.3                                                                           H    H  F Cl OCH(CH.sub.3).sub.2                                                                          glass-like                                 H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CCH  glass-like                                 H C.sub.6 H.sub.5                                                                    H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                                                                  119-121                                    H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CO.sub.2 CH.sub.3                                                                  glass-like                                 H CH.sub.3                                                                           H    H  F Cl O(CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                           glass-like                                 H CH.sub.3                                                                           H    H  F Cl OCH(CH.sub.3)CCH                                                                             glass-like                                 H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CHCH.sub.2                                      H CH.sub.3                                                                           H    H  F Br OEt                                                       H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CH.sub.2 CH.sub.3                               H CH.sub.3                                                                           H    H  F Cl OCH(CH.sub.3)CO.sub.2 CH.sub.3                            H CH.sub.3                                                                           H    H  Cl                                                                              Cl OCH.sub.2 CCH                                             H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CO.sub.2 CH.sub.2 CCH                           H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CO.sub.2 CH.sub.2 CCH                           H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CO.sub.2 C.sub.5 H.sub.11                       H CH.sub.3                                                                           H    H  F Cl CN                                                        H CH.sub.3                                                                           H    H  F Cl OCH(CH.sub.3)CCH                                          H CH.sub.3                                                                           H    H  F Cl OSi(CH.sub.3).sub.3                                       H CH.sub.3                                                                           H    H  F Cl SCH.sub.3                                                 H CH.sub.3                                                                           H    H  F Cl SCH(CH.sub.3).sub.2                                       H CH.sub.3                                                                           H    H  F Cl SCH.sub.2 CHCH.sub.2                                      H CH.sub.3                                                                           H    H  F Cl SCH.sub.2 CCH                                             H CH.sub.3                                                                           H    H  F Cl SCH.sub.2 CO.sub.2 C.sub.5 H.sub.11                       H CH.sub.3                                                                           H    H  F Cl                                                                                ##STR17##                                                H CH.sub.3                                                                           H    H  F Cl OC(CH.sub.3)NOCH.sub.3                                    H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CHNOCH.sub.3                                    H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                                                                  Resin (3                                                                      isomer)                                    H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                         H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CHNOCH.sub.2 CO.sub.2 CH.sub.3                  H CH.sub.3                                                                           H    -- F Cl SCH.sub.2 CO.sub.2 H                                      H CH.sub.3                                                                           H    -- F Cl SCH.sub.2 CO.sub.2 CH.sub.2 CCH                           H CH.sub.3                                                                           H    H  F Cl SCH.sub.2 CO.sub.2 CH.sub.3                               H CH.sub.3                                                                           H    H  F Cl                                                                                ##STR18##                                                H CH.sub.3                                                                           H    H  F Cl OCHF.sub.2                                                H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 C(Cl)CH.sub.2                                   H CH.sub.3                                                                           H    H  F Cl OCF.sub.2 CHFCl                                           H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 CHCHCl                                          H CH.sub.3                                                                           H    H  F Cl OCF.sub.2 CHF.sub.2                                       H CH.sub.3                                                                           H    H  Cl                                                                              Cl NHSO.sub.2 Me                                             H CH.sub.3                                                                           H    H  Cl                                                                              Cl NHSO.sub.2 CH(CH.sub.3).sub.2                             H CH.sub.3                                                                           H    H  H CH.sub.3                                                                         OCH.sub.2 CHCH.sub.2                                      H CH.sub.3                                                                           H    H  H CH.sub.3                                                                         OCH.sub.2 CCH                                             H CH.sub.3                                                                           H    H  F CH.sub.3                                                                         OCH.sub.2 CCH                                             H CH.sub.3                                                                           H    H  F CH.sub.3                                                                         OCH(CH.sub.3)CCH                                          H CH.sub.3                                                                           H    H  F Cl NO.sub.2                                                  H CH.sub.3                                                                           H    H  F CN OCH(CH.sub.3)CCH                                          H CH.sub.3                                                                           H    H  H CN OCH.sub.2 CCH                                             H CH.sub.3                                                                           H    H  Cl                                                                              Cl NHSO.sub.2 NHCH.sub.3                                     H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH.sub.2 CH.sub.3                                H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH(CH.sub.3)CF.sub.3                             H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                       H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                    H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH(CH.sub.3)CCH                                  H CH.sub.3                                                                           H    H  F Cl CO.sub.2 N(CH.sub.3).sub.2                                H CH.sub.3                                                                           H    H  F Cl                                                                                ##STR19##                                                H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH(CH.sub.3)CH.sub.2 SCH.sub.3                   H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           H CH.sub.3                                                                           H    H  F Cl CO.sub.2 CH.sub.2 CF.sub.3                                H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 C(O)CH.sub.3                                    H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 P(O)(OC.sub.2 H.sub.5).sub.2                    H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 P(S)(OC.sub.2 H.sub.5).sub.2                    H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 C(O)N(CH.sub.3).sub.2                           H CH.sub.3                                                                           H    H  F Cl                                                                                ##STR20##                                                H CH.sub.3                                                                           H    H  F Cl OCH.sub.2 C(O)NH.sub.2                                    H C.sub.6 H.sub.5                                                                    H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                               H C.sub.6 H.sub.5                                                                    H    H  H Cl H                                                         H C.sub.2 H.sub.5                                                                    H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                               H C.sub.2 H.sub.5                                                                    H    H  F Cl OCH.sub.2 CCH                                             H C.sub.2 H.sub.5                                                                    H    H  F Cl OCH(CH.sub.3)CCH                                          H CH(CH.sub.3).sub.2                                                                 H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                               H CF.sub.3                                                                           H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                               H CF.sub.3                                                                           H    H  F Cl OCH.sub.2 CCH                                             H CF.sub.3                                                                           H    H  F Cl OCH(CH.sub.3)CCH                                          H C.sub.6 H.sub.4 F                                                                  H    H  F Cl CO.sub.2 CH(CH.sub.3).sub.2                               H CH.sub.3                                                                           H    H  F CN CO.sub.2 CH(CH.sub.3).sub.2                               H CH.sub.3                                                                           H    H  F Cl CHCHCO.sub.2 CH.sub.2 CH.sub.3                            __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________     ##STR21##                                                                                                     Melting                                      R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                             R.sup.4                                                                          R.sup.5                                                                         R.sup.6                                                                           R.sup.8                                                                          R.sup.9                                                                              W point °C.                             __________________________________________________________________________    H  H  CH.sub.3                                                                            CH.sub.3                                                                         F Cl  H  H      O                                              H  H  CH.sub.3                                                                            CH.sub.3                                                                         F Cl  H  CH.sub.3                                                                             O                                              H  H  (CH.sub.2).sub.5                                                                    -- F Cl  H  CH.sub.3                                                                             O                                              H  H  H     H  F Cl  H  H      O                                              H  H  H     H  F Cl  H  CH.sub.3                                                                             O                                              H  H  H     H  F Cl  CH.sub.3                                                                         CH.sub.3                                                                             O                                              H  H  H     H  F Cl  CH.sub.3                                                                         CH.sub.2 CH.sub.3                                                                    O                                              H  H  H     H  F Cl  CH.sub.3                                                                         CH.sub.2 .sup.=                                                                      O                                              H  H  H     H  F Cl  H  CH.sub.3                                                                             S                                              H  CF.sub.3                                                                         H     H  F Cl  H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F Cl  H  H      O                                              H  CH.sub.3                                                                         H     H  Cl                                                                              Cl  H  H      O                                              H  CH.sub.3                                                                         H     H  H Cl  H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  Cl                                                                              Cl  H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  Cl                                                                              Cl  CH.sub.3                                                                         CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F Cl  CH.sub.3                                                                         CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F Br  CH.sub.3                                                                         CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F CH.sub.3                                                                          H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F OCH.sub.3                                                                         H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F CN  H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F CF.sub.3                                                                          H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  H OCF.sub.2 H                                                                       H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F OCF.sub.2 H                                                                       H  CH.sub.3                                                                             O                                              H  CH.sub.3                                                                         H     H  F Cl  CH.sub.3                                                                         CH.sub.2 CH.sub.3                                                                    O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH.sub.2 CH.sub.3                                                                    O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH.sub.2 Br                                                                          O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH.sub.2 F                                                                           O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH.sub.2 Cl                                                                          O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH.sub.2 (CH.sub.2).sub.2 F                                                          O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH.sub.2 CH.sub.2 Cl                                                                 O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH(CH.sub.3)F                                                                        O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH(CH.sub.3).sub.2                                                                   O                                              H  CH.sub.3                                                                         H     H  F Cl  H  CH.sub.2 (CH.sub.2).sub.3 Br                                                         O                                              H  CH.sub.3                                                                         H     H  F Br  H  CH.sub.2 CH.sub.3                                                                    O                                              H  CH.sub.3                                                                         H     H  F Br  H  CH.sub.2 Br                                                                          O                                              H  CH.sub.3                                                                         CH.sub.3                                                                            CH.sub.3                                                                         F Cl  H  CH.sub.3                                                                             O                                              __________________________________________________________________________

                  TABLE 3                                                         ______________________________________                                         ##STR22##                                                                                                                    Melting                       R.sup.1                                                                           R.sup.2                                                                              R.sup.3                                                                              R.sup.4                                                                            R.sup.5                                                                           R.sup.6                                                                            R.sup.8                                                                            R.sup.9                                                                              W   point °C.              ______________________________________                                        H   H      H      H    H   H    H    Cl     S                                 H   H      H      H    F   Cl   H    H      S                                 H   H      H      H    F   Cl   H    Cl     S                                 H   H      H      H    F   Cl   CH.sub.3                                                                           CH.sub.3                                                                             S                                 H   H      H      H    F   Cl   H    H      O                                 H   H      H      H    F   Cl   H    Cl     O                                 H   H      CH.sub.3                                                                             CH.sub.3                                                                           F   Cl   H    H      S                                 H   H      CH.sub.3                                                                             CH.sub.3                                                                           F   Cl   H    Cl     S                                 H   CH.sub.3                                                                             H      H    H   H    H    H      S                                 H   CH.sub.3                                                                             H      H    H   SCH.sub.3                                                                          H    H      S                                 H   CH.sub.3                                                                             H      H    H   H    H    Cl     S                                 H   CH.sub.3                                                                             H      H    H   H    Cl   Cl     S                                 H   CH.sub.3                                                                             H      H    H   H    H    CH.sub.2 CH.sub.3                                                                    S                                 H   CH.sub.3                                                                             H      H    Cl  Cl   H    CH.sub.3                                                                             S                                 H   CH.sub.3                                                                             H      H    F   Cl   H    CH.sub.3                                                                             S                                 H   CH.sub.3                                                                             H      H    F   Cl   CH.sub.3                                                                           CH.sub.3                                                                             S                                 H   CH.sub.3                                                                             H      H    Cl  Cl   H    CH.sub.3                                                                             O                                 H   CH.sub.3                                                                             H      H    F   Cl   H    CH.sub.3                                                                             O                                 H   CH.sub.3                                                                             H      H    F   Cl   CH.sub.3                                                                           CH.sub.3                                                                             O                                 H   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           F   Cl   H    Cl     S                                 ______________________________________                                    

                                      TABLE 4                                     __________________________________________________________________________     ##STR23##                                                                                                    Melting                                       R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                             R.sup.4                                                                          R.sup.5                                                                          R.sup.10   W  point °C.                              __________________________________________________________________________    H  H  H     H  F  H          S                                                H  H  H     H  F  CH.sub.3   S                                                H  H  H     H  F  CH.sub.2 CH.sub.3                                                                        S                                                H  H  H     H  F  CH.sub.2 CCH                                                                             S                                                H  H  H     H  F  CH(CH.sub.3)CCH                                                                          S                                                H  H  H     H  F  CH.sub.2 CHCH.sub.2                                                                      S                                                H  H  H     H  F  CH.sub.2 CCH                                                                             O                                                H  CH.sub.3                                                                         H     H  Cl H          S                                                H  CH.sub.3                                                                         H     H  F  H          S                                                H  CH.sub.3                                                                         H     H  F  CH.sub.3   S                                                H  CH.sub.3                                                                         H     H  F  CH.sub.2 CH.sub.3                                                                        S                                                H  CH.sub.3                                                                         H     H  F  CH.sub.2 CCH                                                                             S                                                H  CH.sub.3                                                                         H     H  F  CH(CH.sub.3)CCH                                                                          S                                                H  CH.sub.3                                                                         H     H  F  CH.sub.2 CHCH.sub.2                                                                      S                                                H  CH.sub.3                                                                         H     H  F  CH.sub.2 OCH.sub.3                                                                       S                                                H  CH.sub.3                                                                         H     H  F  CH.sub.2 OCH.sub.2 CH.sub.3                                                              S                                                H  CH.sub.3                                                                         H     H  F  CH.sub.2 CH.sub.2 CH.sub.3                                                               S                                                H  CH.sub.3                                                                         H     H  F  CH(CH.sub.3).sub.2                                                                       S                                                H  CH.sub.3                                                                         H     H  F  CH.sub.2 CHCHCH.sub.3                                                                    S                                                H  CH.sub.3                                                                         H     H  F  CH(CH.sub.3)CH.sub.2 CH.sub.3                                                            S                                                H  CH.sub.3                                                                         H     H  F  CHF.sub.2  S                                                H  CH.sub.3                                                                         H     H  F  CF.sub.2 CHF.sub.2                                                                       S                                                H  CH.sub.3                                                                         H     H  F  CF.sub.2 CHFCl                                                                           S                                                H  CH.sub.3                                                                         H     H  F  CF.sub.2 CHFCF.sub.3                                                                     S                                                H  CH.sub.3                                                                         H     H  F  CH.sub.2 CCH                                                                             O                                                H  CH.sub.3                                                                         H     H  F  CH(CH.sub.3)CCH                                                                          O                                                H  CH.sub.3                                                                         H     H  F  CH(CH.sub.3).sub.2                                                                       O                                                H  CH.sub.3                                                                         H     H  F  CH.sub.2 CCH                                                                             O                                                H  CH.sub.3                                                                         H     H  Cl CH(CH.sub.3)CCH                                                                          O                                                H  CH.sub.3                                                                         H     H  Cl CH(CH.sub.3).sub.2                                                                       O                                                H  CH.sub.3                                                                         CH.sub.3                                                                            CH.sub.3                                                                         Cl CH.sub.2 CCH                                                                             S                                                H  CF.sub.3                                                                         H     H  F  CH.sub.2 CCH                                                                             S                                                H  H  CH.sub.3                                                                            CH.sub.3                                                                         F  CH.sub.2 CCH                                                                             S                                                H  H  (CH.sub.2).sub.5                                                                    -- F  CH.sub.2 CCH                                                                             S                                                __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________     ##STR24##                                                                                                    Melting                                       R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                          R.sup.4                                                                          R.sup.5                                                                         R.sup.8                                                                          R.sup.9                                                                          R.sup.10  W point °C.                              __________________________________________________________________________    H  H  H  H  H H  H  CH.sub.3  O                                               H  H  H  H  F H  H  CH.sub.3  O                                               H  H  H  H  F H  H  CH.sub.2 CCH                                                                            O 206-208                                       H  H  H  H  F H  H  CH(CH.sub.3)CCH                                                                         O                                               H  H  H  H  F H  H  CH.sub.2 CHCH.sub.2                                                                     O                                               H  H  H  H  F CH.sub.3                                                                         H  CH.sub.2 CCH                                                                            O                                               H  CH.sub.3                                                                         H  H  H H  H  CH.sub.3  O                                               H  CH.sub.3                                                                         H  H  F H  H  CH.sub.3  O                                               H  CH.sub.3                                                                         H  H  F H  H  C.sub.2 H.sub.5                                                                         O                                               H  CH.sub.3                                                                         H  H  F H  H  CH.sub.2 CH.sub.2 CH.sub.3                                                              O                                               H  CH.sub.3                                                                         H  H  F H  H  CH.sub.2 CHCH                                                                           O                                               H  CH.sub.3                                                                         H  H  F H  H  CH.sub.2 CHCH                                                                           O                                               H  CH.sub.3                                                                         H  H  F H  H  CH(CH.sub.3)CCH                                                                         O                                               H  CH.sub.3                                                                         H  H  Cl                                                                              H  H  CH.sub.2 CCH                                                                            O                                               H  CH.sub.3                                                                         H  H  Cl                                                                              H  H  CH(CH.sub.3)CCH                                                                         O                                               H  CH.sub.3                                                                         H  H  F CH.sub.3                                                                         H  CH.sub.2 CCH                                                                            O                                               H  CH.sub.3                                                                         H  H  F CH.sub.3                                                                         H  CH(CH.sub.3)CCH                                                                         O                                               H  CH.sub.3                                                                         H  H  F CH.sub.3                                                                         H  CH.sub.2 CHCH.sub.2                                                                     O                                               H  CH.sub.3                                                                         H  H  F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.2 CHCH                                                                           O                                               H  CH.sub.3                                                                         H  H  F H  H  CH.sub.2 CHCH                                                                           S                                               H  CH.sub.3                                                                         H  H  F CH.sub.3                                                                         H  CH.sub.2 CHCH                                                                           S                                               H  CH.sub.3                                                                         H  H  F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.2 CHCH                                                                           S                                               H  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         F H  H  CH.sub.2 CCH                                                                            O                                               H  CF.sub.3                                                                         H  H  F H  H  CH.sub.2 CCH                                                                            O                                               H  CF.sub.3                                                                         H  H  F H  H  CH.sub.2 CHCH.sub.2                                                                     O                                               H  H  CH.sub.3                                                                         CH.sub.3                                                                         F H  H  CH.sub.2 CCH                                                                            O                                               H  H  H  H  F H  H  CH.sub.3  S                                               H  H  H  H  F H  H  CH.sub.2 CCH                                                                            S                                               H  H  H  H  F H  H  CH.sub.2 CHCH.sub.2                                                                     S                                               H  CF.sub.3                                                                         H  H  F H  H  CH.sub.2 CCH                                                                            S                                               H  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         F H  H  CH.sub.2 CCH                                                                            S                                               __________________________________________________________________________

                  TABLE 6                                                         ______________________________________                                         ##STR25##                                                                                                              Melting                             R.sup.1                                                                            R.sup.2  R.sup.3 R.sup.4                                                                             R.sup.5                                                                           R.sup.8                                                                             R.sup.9                                                                           point °C.                    ______________________________________                                        H    H        H       H     H   F     F                                       H    H        H       H     F   F     F                                       H    H        H       H     F   H     H                                       H    CH.sub.3 H       H     H   F     F                                       H    CH.sub.3 H       H     F   F     F                                       H    CH.sub.3 H       H     F   H     H                                       H    H        CH.sub.3                                                                              CH.sub.3                                                                            F   F     F                                       H    CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                            H   F     F                                       H    CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                            F   F     F                                       H    CF.sub.3 H       H     H   F     F                                       H    CF.sub.3 H       H     F   F     F                                       H    CF.sub.3 CH.sub.3                                                                              CH.sub.3                                                                            H   F     F                                       H    CF.sub.3 CH.sub.3                                                                              CH.sub.3                                                                            F   F     F                                       H    CH.sub.2 CH.sub.3                                                                      H       H     H   F     F                                       H    CH.sub.2 CH.sub.3                                                                      H       H     F   F     F                                       ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR26##                                                                                                                  Melting                         R.sup.1                                                                           R.sup.2                                                                              R.sup.3                                                                              R.sup.4                                                                            R.sup.5                                                                           R.sup.6                                                                            R.sup.7  R.sup.8                                                                            point °C.                ______________________________________                                        H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 CH.sub.3                                                                      H                                    H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 CH.sub.3                                                                      CH.sub.3                             H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                             H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 C.sub.2 H.sub.5                                                               H                                    H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                     CH.sub.3                             H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                     H                                    H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                     CH.sub.3                             H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                     H                                    H   H      CH.sub.3                                                                             H    H   Cl   CO.sub.2 CH.sub.3                                                                      CH.sub.3                             H   H      CH.sub.3                                                                             H    H   Cl   CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                             H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                     CH.sub.3                             H   H      CH.sub.3                                                                             H    H   H    CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                     CH.sub.3                             H   H      CH.sub.3                                                                             H    F   Cl   CO.sub.2 CH.sub.3                                                                      CH.sub.3                             H   H      CH.sub.3                                                                             H    F   Cl   CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                             H   H      CH.sub.3                                                                             H    F   Cl   CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                     CH.sub.3                             H   H      CH.sub.3                                                                             H    F   Cl   CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                     CH.sub.3                             ______________________________________                                    

Formulations

Suitable formulations containing compounds of the formula I can beprepared in the conventional manner, namely as powders, granules,pellets, solutions, suspensions, emulsions, wettable powders,emulsifiable concentrates, et cetera. A great many of these forms can beapplied directly. Preparations capable of being sprayed may be dilutedwith suitable media and sprayed in quantities of between a few andseveral hundred litres per hectare. Highly concentrated preparations areused mainly as intermediate products for other formulations. Theformulations contain, as a rough estimate, between 0.1 and 99% by weightof active substance(s) and at least one representative of the group a)of 0.1 to 20% of surface-active substances and b) of approximately 1 to99.9% of solid or liquid diluents. More precisely, they contain theseconstituents in approximately the following quantities:

    ______________________________________                                                  % by weight                                                                   Active            Surface-                                                    substance                                                                             Diluent   active substance                                  ______________________________________                                        Wettable powder                                                                           20-90      0-74      1-10                                         Suspensions in oil,                                                                        3-50     40-95      0-15                                         emulsions, solutions,                                                         (including emulsifiable                                                       concentrates)                                                                 Aqueous suspensions                                                                       10-50     40-84      1-20                                         Dusts        1-25     70-99     0-5                                           Granules and                                                                              0.1-95      5-99.9   0-15                                         pellets                                                                       Highly concentrated                                                                       90-99      0-10     0-2                                           preparations                                                                  ______________________________________                                         *)Active substance plus at least one surfaceactive substance or one           diluent = 100% by weight.                                                

Lower or higher contents of active substances may of course be present,depending on the intended application and the physical properties.Higher quantitative proportions of surface-active substance: activesubstance are sometimes desirable and are achieved by incorporation inthe formulation or by mixing in the container.

Typical solid diluents are described in Watkins et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwele, N.J. However other solids, either obtained by mining orprepared industrially, may be used. The better absorbing diluents arepreferred for wettable powders and the denser diluents are preferred fordusts, Typical liquid diluents and solvents are described in Marsden,"Solvents Guide", 2nd Ed., Interscience, New York, 1950. Forconcentrated suspensions less than 0.1% are preferred. Concentratedsolutions are preferably stable against phase separation at 0° C. Listsof surface-active substances and their recommended applications arecontained in "McCutcheon's Detergents and Emulsifiers Annuall", MCPublishing Corp., Ridgewood, N.J., as well as in Sisely and Wood"Encyclopedia of Surface Active Agents", Chemical Publishing Co. Inc.,New York, 1964. All formulations may contain smaller quantities ofadditives to reduce foaming, agglomeration, corrosion, the growth ofmicroorganisms, et cetera

The methods for the preparation of these preparations are well-known.Solutions are prepared simply by mixing the components. Finely powderedsolid preparations are obtained by mixing and, conventionally, bygrinding, for exarnple in a hammer mill or jet mill. Suspensions areobtained by wet grinding (see, for example, Littler, U.S. Pat. No. 3,060, 084). Granules and pellets can be prepared by spraying the activesubstance on a preformed granule-shaped carrier or by agglomeration. Inthis connection see J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pages 147 ff, and "Perry's ChemicalEngineer's Handbook", 5th Ed., McGraw-Hill, N.Y., 1973, pages 8-57ff.

For further information regarding techniques of formulation referencemay be made, for example, to the following:

H. M. Loux, U.S. Pat. No. 3, 235, 361, 15 Feb., 1966, column 6,Luckenbaugh, U.S. Pat. No. 3, 309, 192, 14 Mar., 1967, column 5, line 43to column 7, line 62 and examples 8, 12, 15, 39, 41, 52, 53, 58, 132,138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2, 891, 855, 23 Jun., 1959, column3, line 66 to column 5, line 17 and examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons Inc.,New York, 1961, pages 81-96 and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

In the following examples parts are by weight, unless specifiedotherwise.

Example A

    ______________________________________                                        Wettable powder                                                               ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                           80%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             Sodium alkylnaphthalensulphonate                                                                        2%                                                  Sodium lignosulphonate    2%                                                  Synthetic amorphous silicic acid                                                                        3%                                                  Kaolinite                13%                                                  ______________________________________                                    

The constituents are mixed and ground in a hammer mill until all thesolids have on the whole a particle size of less than 50 μm;subsequently they are mixed again and packed.

Example B

    ______________________________________                                        Wettable powder                                                               ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                           50%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             Sodium alkylnaphthalensulphonate                                                                        2%                                                  Methyl cellulose of low viscosity                                                                       2%                                                  Diatomaceous earth       46%                                                  ______________________________________                                    

The constituents are mixed, coarsely qround in a hammer mill and thenground in a jet mill until virtually all the particles have a diameterof less than 10 μm. The product is mixed again prior to packing.

Example C

    ______________________________________                                        Granular material                                                             ______________________________________                                        Wettable powder from Example B                                                                      5%                                                      Attapulgite granules 95%                                                      (USS 20-40 mesh; 0.84-0.42 mm)                                                ______________________________________                                    

A suspension of wettable powder with 25% of solid substances is sprayedinto a double-cone blender; the granules are then dried and packed.

Example D

    ______________________________________                                        Extruded pellets                                                              ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                           25%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             Anhydrous sodium sulphate                                                                              10%                                                  Crude calcium lignosulphonate                                                                           5%                                                  Sodium alkylnaphthalensulphonate                                                                        1%                                                  Calcium/magnesium bentonite                                                                            59%                                                  ______________________________________                                    

The constituents are mixed, ground in a hammer mill and then wetted withapproximately 12% water. The mixture is extruded into cylinders having adiameter of approximately 3 mm, wich are cut into pellets ofapproximately 3 mm in lengt. The latter can be used directly afterdrying; the dried pellets may however be comminuted so that they passthrough the USS No. 20 sieve (apertures 0.84 mm diameter). The granulesremaining behind on the sieve USS No. 40 (0.42 mm diameter aperture) maybe packed for use, while the fine portions are recycled.

Example E

    ______________________________________                                        Granular material of low strength                                             ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                            1%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             N,N-dimethylformamide     9%                                                  Attapulgite granules     90%                                                  (USS sieve 20 to 40)                                                          ______________________________________                                    

The active substance is dissolved in the solvent and the solution issprayed onto dust-free granules in a double-cone blender. After sprayingthe solution, the mixer is allowed to continue running for a shortperiod, after which the granules are packed.

Example F

    ______________________________________                                        Granular material                                                             ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                           80%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             Wetting agent             1%                                                  Crude lignosulphonate (with 5 to 20%                                                                   10%                                                  of the natural sugar)                                                         Attapulgite-clay          9%                                                  ______________________________________                                    

The constituents are mixed and ground until they pass through an 100mesh sieve. This material is then delivered to a fluid bed granulator,where the air current is adjusted so that the material is easily whirledup, with a fine jet of water being sprayed onto the whirled material.Fluidisation and spraying are continued until granules of the desiredsize are obtained. Spraying is then discontinued but fluidisation,optionally with the addition of heat, is continued until the watercontent has fallen to the desired value, generally less than 1%. Thematerial is then removed and the desired particle size range, normallyfrom 14 to 100 mesh (from 1410 to 149 μm) is screened out, after whichit is packed for use.

Example G

    ______________________________________                                        Aqueous suspension                                                            ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                           40%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             Thickener based on polyacrylic acid                                                                   0.3%                                                  Dodecylphenol polyethylene glycol ether                                                               0.5%                                                  Disodium phosphate        1%                                                  Monosodium phosphate    0.5%                                                  Polyvinyl alcohol       1.0%                                                  Water                   56.7%                                                 ______________________________________                                    

The components are mixed and ground together in a sand mill in order toobtain particles having on the whole a size of less than 5 μm.

Example H

    ______________________________________                                        Strong concentrate                                                            ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                            99%                                                 oxa-1,7-diazabicyclo 3.3.0!octane                                             Silicic acid aerogel     0.5%                                                 Synthetic amorphous silicic acid                                                                       0.5%                                                 ______________________________________                                    

The constituents are mixed and ground in a hammer mill in order toobtain a material tha masses through a USS-sieve No. 50 (0.3 mmaperture). The concentrate may, if required, contain other constituents.

Example I

    ______________________________________                                        Wettable powder                                                               ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                          90.0%                                                 oxa-1,7-diazabicyclo 3.3.0!octane                                             Dioctyl sodium sulphosuccinate                                                                         0.1%                                                 Synthetic fine silicic acid                                                                            9.9%                                                 ______________________________________                                    

The constituents are mixed and ground in a hammer mill in order toobtain particles having on the whole a size of less than 100 μm. Thematerial is screened through a USS No. 50 sieve and then packed.

Example J

    ______________________________________                                        Wettable powder                                                               ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                           40%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             Sodium lignosulphonate   20%                                                  Montmorillonite clay     40%                                                  ______________________________________                                    

The constituents are thoroughly mixed, coarsely ground in a hammer milland then ground in an air jet mill in order to obtain particles havingon the whole a size of less than 10 μm. The material is mixed again andthen packed.

Example K

    ______________________________________                                        Suspension in oil                                                             ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                           35%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             Mixture of polyalcohol carboxylic acid esters                                                           6%                                                  and oil-soluble petroleum sulphonates                                         Xylene                   59%                                                  ______________________________________                                    

The components are mixed and ground together in a sand mill in order toobtain particles having on the whole size of less than 5 μm. The productmay be use directly, diluted with oil or emulsified in water.

Example L

    ______________________________________                                        Dust                                                                          ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                           10%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             Attapulgite              10%                                                  Pyrophyllite             80%                                                  ______________________________________                                    

The active substance is mixed with attapulgite and then passed through ahammer mill in order to obtain particles on the whole of less than 200μm. The ground concentrate is then mixed with powdered pyrophylliteuntil homogeneous.

Example M

    ______________________________________                                        Suspension in oil                                                             ______________________________________                                        7-(4-chlorophenyl)-5,5-dimethyl-6,8-dioxo-4-                                                           25%                                                  oxa-1,7-diazabicyclo 3.3.0!octane                                             Polyoxyethylene sorbitol hexaoleate                                                                     5%                                                  Highly aliphatic hydrocarbon oil                                                                       70%                                                  ______________________________________                                    

The constituents are ground together in a sand mill until the particlesize of the solids is less than approximately 5 μm. The resulting thicksuspension may be used directly, but it is preferably used afterdilution with oils or after emulsification in water.

Biological Examples

Experimental results show that the compounds according to the presentinvention are effective herbicides. They are suitable for thebroad-spectrum control of weeds prior to and after the qerminationthereof on surfaces where the entire vegetation is to be kept undercontrol, for example in the vicinity of industrial storage spaces,parking spaces, drive-in cinemas, around advertising hoardings, alongcountry roads and along railways. Many of the compounds are alsosuitable for selective weed control in the cultivacion of rice, wheat,barley, maize, soya beans, sugar beet and cotton.

The quantity to be applied of the compounds according to the presentinvention is dependent on numerous factors, including use as selectiveor as universal herbicides, the respective field crops, the nature ofthe weeds to be controlled, weather and climate, the formulationselected, the method of application, the quantity of foliage plants etcetera. In general the compounds should be applied in quantities beingsuitable for lighter soils and/or soils with a low content of organicsubstances or for instances wheer olny a short reaction period isrequired, for example in the case of herbicides for fallow land.

The compounds according to the present invention may be used incombination with any other commercially available herbicides.

The herbicidal properties of the compounds according to the presentinvention were detected in a series of greenhouse experiments. The testmethods and results are given below. ##STR27## Test Methods

Seeds of Digitaria spp, Echinochloa crus-galli, Setaria feberii, Avenafatua, Bromus secalinus, Abutilon theophrasti, Ipomoea spp., Xanthiumpensilvanicum and sorghum tubers were sown and prior to germination weretreated wiht the test chemicals dissolved in a non-phytotoxic solvent.

In addition these weed species were treated with a preparation intendedfor soils and foliage. At the time of treatment the plants were between2 and 18 cm in height. The treated plants and the control plants weremaintained in the greenhouse for 16 d, after which all samples werecompared with the control plants and the effect of the treatment wasassesed visually. The assessments summarised in Table A are on anumerical scale from 0=without damage to 10= complete annihilation.

The descriptive symbols shown have the following meanings:

C=chlorosis/necrosis

P=burning

H=effect on development

E=retardation of germination

G=promotion or growth

                                      TABLE A                                     __________________________________________________________________________    Application after germination (dosage 2 kg of active substance/ha)                     Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                       1  2  3  4  5  6  7  8  9  10 11 12 13 14 15 16 17 18                __________________________________________________________________________    Echinocloa c. -g.                                                                      2B 2B 1B 1B 1B 1B 2B 7B 2B 10B                                                                              2B 9B 10B                                                                              9B 10B                                                                               9 10 3                 Bromus secalinus                                                                       1B 1B  0  0  0  0 1B 2B 1B 10B                                                                              1B 5B  9B                                                                              9B 10B                                                                              -- -- --                Xanthium pens.                                                                         1B 1B  0  0  0 2B  0 1B 1B -- -- -- -- -- -- -- -- --                Ipomoea spp.                                                                           4B 6B  0  7G,                                                                              3G,                                                                              5G,                                                                              0 8B 6B 10B                                                                              8B 10B                                                                              10B                                                                              10B                                                                              10B                                                                              10 10 10                                  2C 1B 2C                                                    Sorghum  2B 2B 1B 1B  0 1B 1B 3B 2B 10B                                                                              3B 8B  9B                                                                              4B 10B                                                                              10 10 8                 Setaria feberii                                                                        1B 1B  0 1B  0 1B 1B 7B 1B 10B                                                                              3B 9B 10B                                                                              10B                                                                              10B                                                                              10 10 6                 Digitaria spp.                                                                         1B 1B 1B 1B 1B 1B 1B 7B 2B 10B                                                                              3B  9B,                                                                             10B                                                                              9B 10B                                                                              10 10 7                                                           6H                                  Abutilon th.                                                                           2B 1B  0  0  0 5B 1B 8B 7B 10B                                                                              4B 10B                                                                              10B                                                                              10B                                                                              10B                                                                              10 10 6                 Avena fatua                                                                            2B 2B  0 1B 1B 1B 1B 3B 2B 10B                                                                              2B 6B  9B                                                                              9B 10B                                                                              10 10 7                 __________________________________________________________________________

                                      TABLE B                                     __________________________________________________________________________    Application prior to germination (dosage 2 kg of active substance/ha)                  Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                                                                             Cpd.                       1  2  3  4  5  6  7  8  9  10 11 12 13 14 15 16 17 18                __________________________________________________________________________    Echinocloa c. -g.                                                                      0  0  0  0  0  0  0  6H  0  9C                                                                              4C  9C                                                                              10C                                                                               9C                                                                              10C                                                                              -- -- --                Bromus secalinus                                                                       0  0  0  0  0  0  0  2G 1C  9C                                                                              3C  8C                                                                               9C                                                                               9C                                                                              10C                                                                              -- -- --                Xanthium pens.                                                                         0  0  0  0  0  0  0  2G  0 -- -- -- -- -- -- -- -- --                Ipomoea spp.                                                                           0  0  0  0  2G 0  0   0 1C 10C                                                                              4C 10C                                                                               9C                                                                              10C                                                                              10C                                                                              10 10 9                 Sorghum  0  0  0  0  0  0  0   0 1C 10C                                                                              2C 10C                                                                               9C                                                                               8C                                                                              10C                                                                              10 10 7                 Setaria feberii                                                                        0  0  0  0  0  0  0  9H  0 10C                                                                               7C,                                                                             10C                                                                              10C                                                                              10C                                                                              10C                                                                              10 10 9                                                        3H                                     Digitaria spp.                                                                         0  0  0  0  0  0  0  9H 1C 10C                                                                              6C  9C                                                                               9C                                                                              10C                                                                              10C                                                                              10 10 7                 Abutilon th.                                                                           0  0  0  0  0  0  0  10C                                                                              1C 10C                                                                              10C                                                                              10C                                                                              10C                                                                              10C                                                                              10C                                                                              10 10 7                 Avena fatua                                                                            0  0  0  0  0  0  0   0 1C  9C                                                                              1C  9C                                                                               9C                                                                               8C                                                                              10C                                                                              10 10 3                 __________________________________________________________________________

                  TABLE C                                                         ______________________________________                                        Application after germination (dosage 0.2 kg/ha)                                         Cpd.   Cpd.    Cpd. Cpd.  Cpd.  Cpd.                               Object     10     12      13   15    16    17                                 ______________________________________                                        Maize      9B     2B      2B   6B    5B    5B                                 Wheat      4B     2B      3B   7B    5B    7B                                 Echinocloa c. -g.                                                                        9B     3B      9B   10B   8B    9B                                 Xanthium pens.                                                                           7B     --      --   --    6B    4B                                 Ipomoea spp.                                                                             10B    8B      9B   19B   8B    8B                                 Sorghum    4B     2B      3B   7B    7B    7B                                 Setaria feberii                                                                          7B     4B      6B   10B   8B    9B                                 Digitaria spp.                                                                           3B     2B      3B   9B    8B    7B                                 Abutilon th.                                                                             10B    9B      9B   10B   9B    10B                                Avena fatua                                                                              3B     2B      3B   7B    5B    5B                                 ______________________________________                                    

                  TABLE D                                                         ______________________________________                                        Application prior to germination (dosage 0.2 kg/ha)                                      Cpd.   Cpd.    Cpd. Cpd.  Cpd.  Cpd.                               Object     10     12      13   15    16    17                                 ______________________________________                                        Maize      1C      0       0   2C    6H    6H                                 Wheat       0      0      2G   1G    2C    2C                                 Echinocloa c. -g.                                                                        1C     1C      6C   10C   9H    9H                                 Xanthium pens.                                                                           7B     --      --   --    2H     0                                 Ipomoea spp.                                                                             3C     1C      7C   10C   5H    10E                                Sorghum    1C      0      2C   4C    8H    5G                                 Setaria feberii                                                                          9C     6C      7C   10C   10H   10H                                Digitaria spp.                                                                           9G     3C      4C   10C   10H   10H                                Abutilon th.                                                                             10C    10C     10C  10C   10C   10C                                Avena fatua                                                                              2C     1C       0   4C    7H    7H                                 ______________________________________                                    

We claim:
 1. Anellated (oxa)hydantoins of the formula I, ##STR28## wherein R¹ and R², independently of one another, represent hydrogen or a radical from the series (C₁ -C₄) alkyl, (C₁ -C₂) haloalkyl or phenyl optionally fluorine-substituted,R³ and R⁴, independently of one another, represent hydrogen, (C₁ -C₄) alkyl phenyl, both optionally fluorine- and/or chlorine-, bromine- or methyl-substituted, or (C₁ -C₄) alkoxy; or also together form a carbocyclic ring which may optionally be (C₁ -C₄) alkyl-substituted, Q represents ##STR29## wherein W represents S, R⁵ represents hydrogen or halogen, R⁸ represents hydrogen, (C₁ -C₃) alkyl, (C₁ -C₃) haloalkyl or halogen, R⁹ represents hydrogen, (C₁ C₃) alkyl, (C₁ -C₃) haloalkyl or halogen; or if Q is Q-2 or Q-6, R⁸ and R⁹ together with the carbon atom to which they are bonded can be C═O; R¹⁰ represents (C₁ -C₆) alkyl, (C₁ -C₆) haloalkyl, (C₂ -C₆) alkoxyalky, (C₃ -C₆) alkenyl or (C₃ -C₆) alkynyl.
 2. Anellated (oxa)hydantoins of the formula I according to claim 1, characterised in that at least one of the radicalsW represents S, R⁵ represents hydrogen or halogen, R⁸ represents hydroen (C₁ -C₃) alkyl or (C₁ -C₃) haloalkyl, R⁹ represents hydrogen (C₁ -C₃) alkyl or (C₁ -C₃) haloalkyl, if Q is Q-2 or Q-6, R⁸ and R⁹ together with the carbon atom to which they are bonded can be C═O; R¹⁰ represents (C₁ -C₄) alkyl (C₁ -C₄) haloalkyl, (C₂ -C₄) alkoxyalkyl, (C₃ -C₆) alkenyl or (C₃ -C₆) alkynyl.
 3. Anellated (oxa)hydantoins of the formula I according to claim 1, characterised in that at least one of the radicalsW represents S, R⁵ represents hydrogen, fluorine or chlorine, R⁸ and R⁹, independently of one another, represent hydrogen, (C₁ -C₂) alkyl or (C₁ -C₂) haloalkyl, R¹⁰ represents (C₁ -C₂) alkyl, (C₁ -C₂) haloalkyl, (C₃ -C₄) alkenyl or (C₃ -C₄) alkynyl.
 4. Anellated (oxa)hydantoins of the formula I according to claim 1, characterised in thatR⁵ represents fluorine or chlorine.
 5. A herbicidal composition, characterised by havinq an effective content of a compound of the formula I according to claim 1 and a carrier for that.
 6. A method for controlling noxious plants, characterised in that a herbicidally effective quantity of the compound according to claim 1 is applied to the noxious plants or to their environment. 